Jess and Me Pt. 01

This is going to be the first of my real-life experiences over the last 17 years between Jess who was my girlfriend, my fiancé, my Ex, my affair and now my girlfriend again. It is a complex 17-year love saga, and I won't bore everyone with the ins and outs of why our status changed so many times over those year but instead focus on relevant sexual experiences along the way. It is interesting as I started to write these stories how insane our sex life was in the beginning and how we were brought back together time and again by our understanding of each other's fetishes and how we never fully found acceptance for our proclivities in other people. It is a driving force to who we are as people, and it was/is the foundation to our relationship.

These stories are going to focus on a variety of topics. They will develop in the order they developed between us and cover everything from nudism, threesomes, lesbianism, hot wife, cuckolding, massage, but most of all you will see that cock size and exhibitionisms are the main theme in our stories. Those topics are the foundation of what propelled our sexual relationship all these years. Some of these topics you may not enjoy as much as others would, but I want these stories to be authentic and that requires opening the doors to each proclivity in the order we did. I don't think if we had gone about this any other way, we would have built the faith and understanding of each other's fetishes and turn-ons quite the way we have over the years.

Cock size and exhibitionism really is the foundation that everything else launched from so these stories put quite a bit of emphasis on those topics, and rightfully so. Jess was already an exhibitionist before we met. She dabbled in it and knew she enjoyed it but never was encouraged to explore it. We will explore that side of her more in story two to keep with the timeline. As you will learn, Jess is quite young at the beginning of these tales. She is only 20 when this first story takes place. I was a much more mature 32. Naturally I had much more to bring to the party in ways of experience and I think this was a really good thing for us. But as far as exhibitionism goes, I have always been a voyeur and loved staged exhibitionism (the art of exposing oneself in a way that is teasing to the other individual and maybe even they believe that you don't know you are exposing yourself to them when you really are doing it for your own turn on). I helped Jess explore this and encouraged her to open herself up to enjoying the beauty of her body well beyond how she did when we first met.

The other foundational fetish, cock size, really set the table for us to open up to one another. I have always had a cock size fetish. I am not bisexual, but I have always been obsessed by cock size, fascinated by men with large cocks and focused on my own lack of size. I am what the studies would say average in length and a little above average in girth. But, as a big guy being 6'5" tall and a fit 230 lbs., my big frame dwarfs my "averageness". Also, my penis never hangs down when I am soft. It always stays pulled up mostly looking might short with no swing to it at all (a grower not a show'er as they like to say). This has always been something I have fixated on over the years, but I never really explored it the way Jess and I did, and I never had a partner that went with it the way she did/does so from that perspective much of this was new to me.

Before I move on with the story (what you came her for) I will give you some more visuals on Jess. As I said, Jess was just a couple month shy of her 21st birthday when this story takes place. We worked for the same company which is how we me. She worked in the medical facility, and I was an executive with the company in the front office. She would wear baggy scrubs, always had her hair up and kept a low profile while at work. Don't get me wrong she is absolutely gorgeous, but if you're just passing by, as I often did, you might not really take notice unless you had to ask her a question or ended up in an elevator together. I was very focused at work so my heads down all business presences caused me to miss out on the best thing at work for a couple years. She actually started working for us as a high school student. It was the Company Holiday party where I definitely took notice of this stunning beauty.

She was in tight hip hugger jeans, a tight shirt that showed off her 36C very high and firm tits showing plenty of cleavage. Her hair was done, some light makeup on (she never wore much makeup) and man was she looking amazing. She was just plain hot. I literally stopped in my tracks and to be honest, I didn't even know who she was. I asked a coworker, and they said her name was Jess and worked in medical. I was stunned that someone that looked like her and I never noticed her. Over time I started describing her as looking like a Playboy Model to put the right context in peoples mind if they did not know her. We went to a formal even and she was in a long formal dress that clung to her sexy body, literally nothing on underneath the dress, hair and makeup professionally done... she looked like she belonged on the red carpet at the Oscars. She was absolutely stunning, and she knocked me off my feet that night

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 that first Cancun vacation when Jess was standing by herself drinking a glass of wine waiting for me. I was about 50 feet away talking to someone and the guy looked at me and said, "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.

As C.W. from Mythic Quest will tell you, backstory is everything but enough with the backstory already. Let's get on with the story.

The first part of this first story is literally taken from an email exchange that occurred between Jess and I about 6 weeks into dating. I cut out all the email header information and left the conversation. Cleaned it up a bit for reading purposes but the context and wording is literally how the conversation went. The subsequent story of the follow up stuff that happened the night after the email exchange is to the best of my recollection. Most of these early stories will be in this format because this is how it happened. We would email all day and explore or fantasies, plan things and then we would bring that vibe home with us into the bedroom.

As I said this story is 6 weeks into dating. Jess and I started talking 2 weeks after she broke up with the Christmas Party guy who was named Mike. I hope you like.

Me: "So, when we were watching porn in Cancun You were really getting turned. What was your favorite part about that?"

Jess: "It was just a lot of fun. I have not really ever watched porn with a boyfriend before."

Me: "What was your favorite part about that?"

Jess: "It was just fun watching them get it on while we were playing too."

Me: "Did you like the girl-on-girl stuff?'

Jess: "Yes, it was very hot."

Me: "Have you ever been with a girl?"

Jess: "LOL. No not really. I have made out with Kristy before when we were drunk at a party but that really is it."

Me: "You really seemed to like the last one we watched. The one with the wife hooking up with her husband's friend."

Jess: "That one was hot."

Me: "I could tell. You got so wet, and you came sever times during that one. What did you like about that one?" (We were fucking and then using her vibrator on her too while we were watching)

Jess: "It was just hot watching them."

Me: "Tell me more! Any part in particular?"

Jess: "LOL. I don't know. I guess liked it when she was on top of him."

Me: "What did you like about that?"

Jess: "I don't know. LOL It was just hot watching her ride him."

Me: "Did you like watching her slide up and down on his big cock?"

Jess: "Yes. What part did you like?"

Me: "I liked when he took her from behind. I liked the way his cock looked going into her. What else did you like about it?"

Jess: "I just thought it looked really hot."

Me: "Did you like how big his cock was?"

Jess: "LOL. Well yeah. Nobody likes small ones in porn."

Me: "He was really big."

Jess: "LOL. Yes, he was."

Me: "What did you like about his cock?"

Jess: "I don't know. It just looked hot."

Me: "Did you like how long it was more or did you like that it was so thick?"

Jess: "Oh boy. LOL. You are cracking me up. Both I guess. I just liked the way it looked when she was on top of him riding him."

Me: "What part did you like about that?"

Jess: "I liked how she would slide up and down on him."

Me: "You mean like it was long enough where she could do that?"

Jess: "Yeah, I guess so."

Me: "Did you like how her pussy looked stretched around it?"

Jess: "Probably hurt. LOL"

Me: "Have you ever been with someone that big?"

Jess: "No."

Me: "What were your ex's like?"

Jess: "What do you mean?"

Me: "Did anyone have a big cock?"

Jess: "I don't know. You know I haven't been with that many guys."

Me: "I know. But you have had boyfriends. You dated, Mike before me and there was Derek and Joe that I know about. You dated all of them for at least a few months and Joe for several years so I would assume you had sex with them."

Jess: "Yeah, I guess so."

Me: "Was there anyone else?"

Jess: "Are you sure you want to know? You probably will think I'm a slut."

Me: "Not at all. We both had a history before we met. I like talking about this stuff. I like knowing what you did, what it was like, what you like, what turns you on. I don't judge stuff like this. If anything, it just turns me on."

Jess: "Why does it turn you on?"

Me: "I just like hearing about what you have experienced, what things were like for you. What you thought about something, what was going through your mind, trying to understand your experience and what it was like for you. That is a big turn on to me."

Jess: "Even if it's about other guys? I don't think any other guy I have dated would be happy that I slept with other people."

Me: "Yes. I am not worried about it. That is actually ridiculous being jealous over someone's history. I am the opposite, I like knowing, I want to know what it was like for you, what turned you on, what you didn't like, the more I know about those things the more open we will be sexually and enjoy what we have. If something really turned you on, I want to know so I can do it, use that in our sex life."

Jess: "Well, I don't think I want to know about your ex's. Sorry."

Me: "LOL. That is fine, I won't talk about them unless you ask. Fair?"

Jess: "Ok, thanks."

Me: "So, what were your ex's like? Did they have big cocks?"

Jess: "You really want to know this stuff?"

Me: "Absolutely."

Jess: "Well, I have only been with 3 people, so I don't have a lot of experience. Derek was really small."

"Oh really? How small?"

Jess: "Like really small. Like the size of my thumb."

Me: "Yikes. That is small. Was the sex good at least? LOL"

Jess: "LOL, NO. He came really fast, and I really couldn't feel it that much. We only had sex like twice thank God. He was always such a drunk idiot. I don't know why I was even dating him."

Me: "What about the other ones? What were they like?"

Jess: "God, I don't know. I didn't measure them or anything."

Me: "LOL. Of course not, but would you say they were big, medium, small?"Jess:

Jess: "Big I guess."

Me: "Oh really? Like how big?"

Jess: "Are you sure you want to know this stuff? I don't want to hurt your feelings or get into a fight or something. This is so strange to talk about this with you."

Me: "You are not going to hurt my feelings. I said I like hearing about this stuff. I have a bit of a chubby right now. Turns me on."

Jess: "LOL."

Me: "Who was bigger? Joe or Mike?"

Jess: "Mike"

Me: "Was he just longer or thicker or both?"

Jess: "OMG, you are cracking me up. Both"

Me: "But Joe was still "big"?"

Jess: "Yeah, I guess so. It's not like I have a lot to compare to."

Me: "What about me? What am I?"

Jess: "Oh gosh!"

Me: "Well, was Joe bigger than me?"

Jess: "Babe, I love your penis. I love having sex with you. It's perfect for me."

Me: "I know you do. We have great sex. I know I can make you cum. I am just curious is all and I want to know the truth. You won't hurt my feelings. So, what about me then?"

Jess: "I don't know. Medium, I guess. Average probably."

Me: "So, Joe was bigger?"

Jess: "Babe!!"

Me: "It's ok, this kind of stuff turns me on hearing about it."

Jess: "Really?"

Me: "Yeah, I like knowing this stuff and what is in your head. What you think. It turns me on."

Jess: "Ok. Well, I am trusting you on this then because I really don't want to ruin anything."

Me: "It won't. It will make us stronger if we can be honest and open about this stuff. That is why I really want you to give me honest answers when I ask you about stuff like this. You're not going to hurt my feelings."

Jess: "Ok babe. I love that about you."

Me: "Ok, so Derek was smaller than me, right?"

Jess: "Oh god yes. It was so small. Ehh."

Me: "LOL. Were you surprised I did not have a big cock? Be HONEST!"

Jess: "A little."

Me: "Were you disappointed."

Jess: "Not disappointed. Surprised is all."

Me: "Why were you surprised?"

Jess: "I don't know. You are such a big guy so I guess I kind of assumed it would be really big. I just remembered being surprised is all."

Me: "I have heard that before. I am a big guy, and everyone assumes I am going to have this massive cock."

Jess: "Yeah, that is what I thought too. LOL Sorry."

Me: "No need to be sorry. So, I was bigger than Derek and smaller than Joe and Mike?"

Jess: "Yes"

Me: "How much smaller?"

Jess: "Babe, it's not like I was paying that close attention and Joe was a long time ago. Are you sure you really want to talk about this stuff? I have never talked about anything like this with a boyfriend before."

Me: "I am positive. Not only do I want to know, but I also like it. Do you think that is weird?"

Jess: "Not weird it's just different. Definitely new for me."

Me: "I also want you to be brutally honest. I want you to not be afraid of hurting my feelings. You have to promise me that."

Jess: "Ok. I will try to be, but you must promise me that this type of talk will not ruin things. It really worries me to talk about my Ex's like this. I have dated jealous people before, and I do not do well with jealousy."

Me: "I promise you with all my heart. You just promise me back that you will always just tell me the truth, exactly what you remember or exactly what you think about something. Do not hold back just be honest."

Jess: "Ok. I promise."

Me: "So, can I keep asking you questions? Are you ok with this?"

Jess: "Yes, for a little bit. Then I have to get back to work you pervert!"

Me: "LOL. How much bigger than me were they?"

Jess: "If I had to say, Joe was a little bigger and Mike was a lot bigger."

Me: "Was Joe longer or thicker than me or both?"

Jess: "He was definitely longer and a little thicker."

Me: "How much longer do you think? Like an inch?"

Jess: "Maybe an inch longer or maybe an inch and a half. I don't really know but it was definitely longer."

Me: "Wow is quite a bit longer."

Jess: "I'm sorry, you told me to be honest. See now you're taking it wrong. I don't care and I love your penis its perfect for me."

Me: "Oh no it did not hurt my feelings or anything. It's kind of exciting because that means Mike is even bigger than that?"

Jess: "LOL. Yes, I guess so. He was the biggest I slept with."

Me: "How much longer do you think Mike was then I am?"

Jess: "I honestly don't know. Mike was just very big."

Me: "But not as big as the porn star in Cancun?"

Jess: "I don't know. Maybe not that big but he was big."

Me: "Well let's see, if Joe was 1.5-2 inches longer do you think Mike was 3 inches longer? Or more?"

Jess: "I don't know in inches but if I am being honest, it was a lot longer then you are. He was very long."

Me: "Was he thick also?"

Jess: "Yes."

Me: "How much thicker than me?"

Jess: "I am doing my best to be honest here but still a bit nervous. You are asking for details, and I am afraid of TMI. It's not like I am just saying it was big and you are like, oh that is cool. You want more details than girls ask for in drunk girl talk at the bar! LOL."

Me: "Because I want to know. It's the details that count to give me a mental picture of what it was like. You were there so you know in your mind everything. If you just tell me, it was big I don't really understand what you know. If you tell me, it was as small as my thumb. Now I have a much better idea of how small Derek was because I can imagine a penis the size of your thumb. It's the comparison that helps me visualize it."

Jess: "That was different because it was so small. That is what I told Kristie after Derek and I broke up that he was as small as my thumb. That is what came to mind when you asked."

Me: "Yes, but it worked. If that is accurate on his size it gave me a great mental picture. I also know you didn't like it because it was too small."

Jess: "It really was."

Me: "Are you still nervous giving me answers?"

Jess: "A little. It's just I don't know; it was as big as a big cucumber. LOL"

Me: "Well, that is no fun. That does not help me visualize it. All, common play with me. How much thicker than me was he? Help me understand. I already know he was a lot bigger so help me understand. It's hot."

Jess: "What is hot about it?"

Me: "You got to fuck a big cock like that! That is hot! It's fun to think about."

Jess: "You crack me up. I did not expect that response at all."

Me: "So, tell me? How much thicker? You told me about Joe so tell me about Mike now?

Jess: "Ok. But I don't want to sound mean is all. If I am being honest, he was like twice as thick as you are. I can wrap my hand around you and my fingers go all the way around no problem. I just remember that my fingers did not touch each other when I wrapped my hand around his. There was a space between my fingers and my thumb. What stuck in my mind was the first time we had sex. I obviously already knew he was big as I had rubbed it over his pants but as we got into it, I went down on him first. It in his living room and the TV was on so the room was lit, and I could clearly see what I was doing. I just remember seeing my hand and thinking, my god my fingers don't touch. When you asked me about how thick hew was that was the image that popped into my mind. I was embarrassed and shy to just say that because that is what I remembered and what popped into my head. Kind of embarrassing."

Me: "That is so hot! And that is what I was wanting you to do. To share everything. Every thought. Please try too not be embarrassed. You're not going to shock me or turn me off or make me mad or anything like that. Just hearing what you really think and what went through your mind is such a major turn on for me. And that is a really hot one! So, it must have been quite a bit of difference going from Mike to me since you had only broken up with Mike like a month before we had sex."

Jess: "Yes."

Me: "Just, yes? Common you went from what is obviously a huge cock to a medium/average one. Common, that had to be quite a bit different at first since were used to his size?"

Jess: "LOL. Ok babe. I am really trying here. This is very new for me. Mike was so jealous all time and he could be cruel too. He made me feel so weird about things. This being open is really nerve-racking and VERY new to me. Especially talking about my ex-boyfriends' cock size! This is the last thing I thought we would talk about today."