Understand

This is an original fictional story portraying characters that are well over the legal age of consent. The material explores trust, love, kink, and BDSM. These are the first two chapters of a work in progress. Both positive and negative comments are encouraged and welcomed.

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Chapter One, Honesty

I woke up earlier than usual this morning. The anticipation of my five-thirty appointment has me excited and a bit nervous as well. Most ladies have had their hair removed at a wax salon, many do it routinely. Like many men, I trim my pubic hair. Most women appreciate the gesture. She is considerate enough to keep herself hair free for my pleasure. Occasionally I shave it all off, and I mean everything. It is actually fairly easy to shave your cock and balls. You just need a new razor and some creamy body wash or lotion. Stretch the skin, shave with the grain, and go slow and careful.

I feel a little weird about my decision to get waxed and still might call it off at the last moment. Being completely smooth for weeks without any daily maintenance is appealing though. My girlfriend is out of town and doesn't know my plans. I generally tell her everything and keeping a secret feels wrong, but doing this as a surprise should be fun. Bridget gets pretty excited when I shave completely. One time, when I was really smooth, she didn't allow my cock out of her mouth for what seemed like an hour. If you can endure the intense tickle sensation that occurs when your woman keeps stimulating you past orgasm it really is worth it.

Most guys cannot handle it and make their partner stop before it really starts feeling good. You may have to be restrained to achieve this, without pulling away and making her stop. Most women experience a similar sensation right after orgasm and will make you stop as well. If this sounds familiar, hold on tight and keep going the next time. She will yell stop and struggle but she will not get mad at you. Trust me! More on this later...

Our friendship began about three months ago, yet we have "officially" been a couple for only a few weeks. Our relationship started one evening as she was having difficulty locking up the booth she works in. She called over to me and asked for help. I kinda knew her in passing but had never said anything besides "hi". I helped her by pulling up on the door so the lock could operate. She thanked me with a hug and a peck on the cheek and introduced herself.

She told me she could tell I was staring at her every night as I passed by. I admitted to the crime and added the fact, that I was actually stalking her and knew where she lived. Also that I also watch her run by every morning from my upstairs window and how I enjoy seeing her in booty shorts and a bra top or other revealing outfits. I told her, now that she knew I was a pervert, she could slap me and run away. She told me she would not be running away as she was also guilty of watching my booty go by and was stalking me with the help of my friends.

We spent the next hour sharing "secrets" and coming clean about how both of us have been adjusting our habits to get near each other. Neither one of us realized how obvious our actions were. Bridget had been pulling up on that door, by herself, to lock it for months. You do understand we already had feelings for each other. We just didn't know it yet.

My name is Jake. I am the host on the Discover Key West, Double Decker Tour Bus and back then Bridget worked at one of the outdoor kiosks that books adventures for tourists. I have lived on this island most of my life. I did spend four years in Jacksonville, at Florida State, playing football. Unfortunately an injury cut that short but I did end up finishing school. That was almost twenty years ago.

I've worked in the family business ever since. We have a couple of tour buses and also own four boats that we charter for sightseeing and fishing. Most of our "employees" are family members or close friends. Officially there are four owners including my Uncle, my Brother and Sister, and Myself. We all do jobs that interact with our clients rather than sit in an office somewhere. We have a staff that does the boring stuff like keeping the books and maintaining the fleet. My dad and his brother founded the business that way, so as not to lose touch with our customers. My dad passed away several years ago. My Mom receives income from the business but is re-married and lives in California.

Bridget is about ten years younger than me and very fit. She has one of those booties that swallows up leggings and leaves little to the imagination on what is underneath. There is a bit of space between her legs and you can see the definition of her labia when she walks away from you. She has what some people might call "Child Bearing Hips". Men are instinctively attracted to this shape. The rest of her body is a perfect match to her butt, with a fairly skinny waist, nice size boobs and super long legs. She is only a couple inches shorter than me.

Her skin is silky smooth and her hair is blond and shoulder length. Her face is hard to look away from and her smile just captivates me. I don't think she even knows how to frown. Bridget has an infectious positive attitude and is extremely confident. I was attracted to her from the moment I first noticed her. I approach women all the time but never tried to talk to her. Maybe I thought she was out of my league or the age difference intimidated me.

She looks like a supermodel while I am pretty average with a slight beer belly. I was terrified to make the first move. I am grateful she had the courage to do so. From the moment we met, we just started telling each other everything. We got into the routine of sharing every detail about our feelings, fears and desires. Two weeks into our relationship I said, "You do understand I will likely ask you for sex someday." She responded matter-of-factly, "You do understand I will probably say yes."

The sex eventually happened but ironically I did not ask her for it. For almost 3 months our relationship was very casual. We were dating other people and treated each other more like friends than lovers. Our routine was to use each other for sexual release in dry spells and genuinely kept it free of jealousy. We would tell each other about our other dates, with others, including pretty much every fact including how they kiss, what they look like naked and if they had a clue about pleasing us in bed.

We went into great detail, literally blow by blow including who was getting blown. I think the full disclosure is what kept us from becoming possessive and jealous. There was no possibility of having any bad feelings because we literally knew everything about each other. Without any pact or agreement we just shared everything immediately and honestly. It was like the conversations you would have with your best, same sex, bud.

Our stories were so explicit that we often got really turned on but we didn't take it any further at first. There were no secrets kept about our arousal but we just chose not to act on it. We would often share how turned on we were, hug goodnight and then go to our separate beds. The most that would happen was holding hands and sitting close to each other. We didn't really kiss for almost a month except for a peck on the cheek or a very quick touch of the lips.

Our conversations took place several times a week and often lasted for hours. Our friends were absolutely certain we were already having sex. As I mentioned. Bridget had elicited their help, to find out more about me, without my knowledge. This occurred long before the kiosk locking ruse. By all appearances we were already a couple. As time went by we tended to be together almost every evening after work, sitting outside, holding hands and learning about at each other.

The first time we hooked up it took me by complete surprise. We had been hanging out together for about a month. Although I had told her early on that I would eventually ask her for sex our non-stated understanding moved us into the direction of taking things really slow. We were just buddies telling stories and supporting each other with no judgement. We were sitting on the corner of Whitehead Street and South close to our homes. I live in a historic home that has been in my family for generations. It is significant because it's built on the southernmost area of the United States. Our whole block is designated as a national landmark and the house next door is a public museum. It is literally the southernmost structure in the U.S.

Whitehead Street cuts across the tip of the island and terminates at the ocean at both ends. The Northern tip of Whitehead Street is where the giant cruise ships dock, about a dozen blocks away. Bridget lives in an upstairs apartment, in the center of town, near the former home of Earnest Hemingway. Our city is full of history and bustles with tourists, but has a very small town feel in the eyes of the locals. I think this is true of most any resort area.

Bridget was telling me about her date the night before. She had high hopes for this guy as her recent relations had all been one night things with poor follow up from the guys. My recent history was similar. It's not entirely a bad thing but it's more interesting to explore someone sexually over a period of time. One night sex is fun but quite sterile and empty, afterwards. It also requires a sizable condom budget. Bridget apparently has quite a libido.

She had orgasm stories almost every evening after work and most did not involve a second person. I'm pretty sure if I was in her apartment I could identify and locate all of her dildos and toys. She was that graphic in her descriptions. The level of arousal during story time was often quite intense. I also had a habit of over sharing. I had been experimenting with some small anal toys and went into great detail without being embarrassed. I was also trying to learn rope-bondage by watching online tutorials. I was practicing with knots and such on myself and told her about how I would tie my own legs in precarious positions and then use a masturbation toy on myself.

Bridget told me I was wasting perfectly good cum and how we needed to find me a real vagina to play with and how self-bondage is actually quite risky. She then recited a list of rules followed by rope practitioners that I had honestly never considered. The most interesting point was having safety scissors handy. I had never considered that. Quite to my surprise Bridget was no stranger to rope bondage. She told me she belonged to a local club where she often taught classes. I had heard rumors of its existence. She offered to sponsor me to become a member if that sounded interesting. I learned that they only accepted new members thru referrals. I didn't ask her the obvious question but assumed this was really a sex club.

A little more about Bridget's date night; she told me he was very good looking and filled the front of his pants very effectively. He had a muscular rear end and a body builder physique. However he ended up being very shy and reserved the whole evening and stumbled through conversation miserably. It fascinated her that he even had the courage to ask her out in the first place. He made zero attempts to touch her or hold her hand and seemed troubled with eye contact. She shared that boredom set in even though he was very pleasant to look at.

Bridget said he finally got up the nerve to kiss her goodnight and immediately got very aggressive with his tongue. She said he literally got her whole face wet and tried to vacuum her tongue out of her mouth. According to her it was gross instead of sexy. When the date started she had every intention of inviting him into her apartment and keeping him awake until breakfast time. That did not happen. I was about to find out what he missed out on.

Bridget announced her lips felt dry. She rummaged thru her purse and found some shimmery lip balm. She applied some to her lips and announced, "You look dry too." It felt very slick as she applied it to my lips. It had a sweet taste and felt very sexy, especially since it had just touched her lips. The weather was hot and humid as is often the case in our neighborhood. We were both a little sweaty. Her skin glistened and her skimpy white cami top was glued to her leaving no contour to the imagination. The local ladies generally skip the bra during summer.

Our climate is almost always tropical. This would probably be a rain forest if the pavement didn't exist. She was wearing a very seductive fragrance that evening and I was overwhelmed with an impulse to bring her closer and kiss her. As always, I resisted the urge. She continued by comparing our frequent conversations, such as this one, to the awkward one last night. She told me how easy I am to talk to and how I always give her my full attention. She also told me she felt safe in my presence and loved how open and honest I was with her. I agreed that our lack of secrets was powerful and liberating.

She then said, "Let me show you how gross that kiss was." My heart jumped, I was pretty certain I was about to kiss my best friend for the first time. We were sitting on a short concrete retaining wall, facing each other and holding both of each other's hands. This was our standard story telling pose. We had agreed that this was a way to reinforce the honesty in our discussions. We would have full eye contact and the hand holding was like a human lie detector. She would normally put her legs over the top of mine but leave about a foot of space between us. I had fantasized about this moment but had never followed thru.

I suppose there was a fear our friendship would change somehow and the sharing of stories would slow down or end or maybe I was just chicken. I had let myself get into a pattern of failing to initiate a kiss, even though conditions were often very favorable. I also had an irrational fear of rejection, for some reason. Bridget scooted her butt forward so we were just barely touching. The grip on my hands tightened as if she was restraining me. She licked her already slippery lips. Then she leaned forward and kissed me very gently.

We did not close our eyes. She moved hear head back and forth to take advantage of our recently lubricated lips. The sensation was overwhelming. I could feel my whole body reacting. Next she suddenly summoned all the spit she could muster and stuck her tongue in as far back in my mouth as it would go. She got my entire face wet and rubbed her saliva everywhere. Then she got a hold of my tongue and sucked so hard that it created pain. It actually hurt the muscles at the back of my tongue. She continued the face washing and even licked my nose. I asked her, "Did he really do that?" ... Let me show you what a first kiss should really feel like."

I went in for the kiss and sucked up her tongue but did it gently like you would do with a woman's clit to make her cum. She immediately went limp and started moaning as if I really had her clit in my mouth. Her reaction to my kiss was incredibly seductive. I lost all my fear and inhibition, in that moment. She let go of my hands and reached behind me pulling me close. I put one hand behind her neck and the other behind her head. I kept sucking on her tongue, pretending it was her clit, progressing to a routine I use on ladies all the time, moving from gentle sucking to circling with my tongue then gentle flicks, and then back around.

I had told her about the technique during one of our, tell all, sex debriefings. She knew what I was doing to her and kept reacting with more sounds of pleasure. She pulled her hips even closer to me and began moving in a grinding motion and eventually wrapped her legs around my body. This is by far my favorite sex position. Face to face with the woman sitting on your lap frees your hands and gives you wonderful access to each other's bodies. It also puts your cock in contact with her G spot very nicely. You can easily play with her clit also.

Too bad we were still dressed. Between the way she smelled, the fact her tongue was actually in my mouth, and her complete focus on me, I lost all sense of reality. The fact we were on a public street was no longer on my mind, at all. We kissed for another ten to fifteen minutes, without saying a word, taking turns pretending something other than our tongues were being worked on. When we finally broke free she got up and took my hand, leading me towards her house which was only a block away. It was common to walk her home after work holding hands. I was very self-conscious as we stood up and also fairly dizzy. My cock was completely stiff with a noticeable wet spot on my light blue shorts. Bridget looked down and giggled as I adjusted myself with my free hand.

Chapter 2, Discovery

Key West is a pretty small community. Getting home from work was a short walk for both of us. Neither one of us spoke. The fact I just kissed my friend for almost twenty minutes actually had me pretty fulfilled. I was totally happy dropping her off, walking back to my house and having some very sexy dreams. We were almost at her door and she stopped to give me a long hug. I thought it only natural to kiss her one more time before saying goodnight. She got really close to me and put both hands near the small of my back. I don't think I realized what was on her mind.

This kiss felt even better than last one. We were into marathon lip lock number two. My hands started on her back and instinctively wandered to her butt cheeks. My cock started getting hard again and I could feel it pressing up against her pussy lips. I was wearing swim shorts with a built in liner. They were kinda baggy with no real support. She was wearing thin leggings and I could feel the contours of her warm entrance. She then wrapped both arms around my neck and pulled her legs up behind my butt.

Bridget re-aligned her pussy with my boner. She was hanging on in a sex position we had talked about in the past. The man has to hold on tight while the woman pretty much controls everything else. I leaned back on the wall behind me for support. This created even firmer contact of our fun parts. If we had been naked I would have entered her almost automatically. I was somehow still convinced this was going to be the end of our night. Bridget said, "Your cock feels pretty big." I started contemplating the walk home and how to hide the bulge in my pants. The streets were still busy with other people. Bridget hopped off of me and picked up her purse. She got out her keys and opened her front door. Maybe I was naïve, but I truly did not expect Bridget's next statement... "You do understand we are going to fuck now."

That night was epic. We actually took things really slow. We went inside her house about ten o'clock. She led me to her bedroom and had me sit on the bed. She had a four post bed with a canopy made out of large wooden timbers. It had a bunch of wrought iron details that included a dozen large round rings that swiveled, kind of like old fashioned door knockers. A blindfold and a rubber ball gag were hanging from one of the rings. On another corner hook, was a shiny black leotard with strategic openings for nipples and pussy.

There was oversize metal hardware everywhere. Drawers circled the base and were surely filled with all sorts of ropes, cuffs, shackles and toys. She had told me some of the things about her bed during story time, including the various sex toys in the drawers, but not that it included so many functional bondage anchor points. A large glass object, on one of the night stands that resembled a brandy snifter but triple the normal size, was filled with a variety of condoms. On the other side was a wicker basket with several small bottles of flavored lube and various cock rings and mini vibrators still sealed in their original packaging.