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."
