Kyle Finds Jen – BDSM


Kyle was 36 and successful but had failed at marriage. He was a good guy, worked hard, and provided for his family over and above what most men could. But something about his marriage was just off. Eventually he figured it out it was a lack of sexual chemistry. What he sought and what his wife sought were very different, and eventually it simply was not enough for either of them.

Kyle wanted to have intense sex, with multiple kinks and enjoyed sharing his partners. Sometimes this was him and his partner inviting another man or men into their sex life for group fun, and sometimes it was Kyle watching his partner. Kyle was entirely straight, and was not sure why he enjoyed seeing his partner with another so much. Through online searches he found cuck porn, which was intriguing but certainly was not him. He liked the bull more than the cuck, but he was more in the cuck position. Close but no cigar.

He kept searching and began gravitating toward bdsm and dom/sub porn and dynamics and researched that. He realized that he was very dominant and that was part of the conflict with his wife. She could not be a submissive woman in a feminine role. Without her submission, he could not be fulfilled in the way he needed. He began realizing that what he enjoyed about sharing his playmates was that he could dominate them by giving them away and choosing their bulls. Then he discovered stag/vixen as a dynamic. A dominant and strong alpha husband who shares his wife because he wants to see her pleasure. Everything made sense. The marriage ended, breaking down somewhat amicably and Kyle began looking for his dream submissive vixen who would be his one and only love while also being committed to being the sexy vixen he craved.

With so many options to choose from as far as dating sites, Kyle was a bit overwhelmed. There were the typical ones that everyone was on, and he got on these just to experience it. Some were made for hooking up, and some were made for getting married. These were hit or miss. He would get a lot of responses, but mostly they seemed to be run of the mill women. Some were certainly gorgeous, and most guys would have been happy to create a great relationship with them. But Kyle knew they were not what he was looking for.

Kyle stumbled on a few potentials. There was Kelsey the psychologist who was truly submissive, but simply not Kyle’s type after about a month. Then there was Sarah who was a very young blonde who Kyle was very interested in and filled the submissive role well, but whose family and political concerns got in the way. There were some one night stands mixed in and those were fun but also not what Kyle wanted. Kyle wanted a real connection with a stable woman in a relationship, but he needed a woman who was sexually confident, experienced, and open to experimentation. Kyle knew that relying on regular dating sites simply was not gonna help him discover the type of girl that he needed.

He began looking around online for alternative dating sites. Then he stumbled on two, one designed for couples to discover individuals to join as a third, and the other just a great conglomeration of swingers. These served the purpose of finding women with sexual experience and confidence, but most were already in relationships and only looking for guys, or “bulls,” to join them for fun. Kyle of course enjoyed meeting these wives, some the husband knew about, some didn’t. Some were great in bed, some weren’t. There was Charlotte who Kyle flew to another city to meet and dominate while her husband was at home completely unaware of the happenings, or Kaitlin who came to Kyle’s house while her husband was deployed in the military. Then there were others, like Amy, whose husband knew but didn’t ask questions, and entirely single women like Cristina who were great but not the submissive Kyle wanted and were outside of an age range that could make a real relations work.

Then a trendy social media platform launched its new dating user account app, and Kyle wondered it couldn’t hurt to try it out. It would mostly be vanilla, but maybe Kyle just needed to give up on his hope of the perfect vixen and just move on from his failed marriage. Again, it was so easy to get matches for Kyle. He was successful, mid-thirties, good looking, and enjoyed the gym. But most of the chats bored him. He stumbled upon one user account, of a woman named Emilia, whose user account picture honestly did not really excite him. But a couple of the other pictures in the user account were very attractive, intrigued Kyle matched and began chatting. He quickly realized that there was more to this particular match and decided to be bold and lay out pretty well what he was seeking and this unknown woman opened up that she was seeking something very similar. Kyle and Emilia began dating and became very serious but over the course of the next two months it became apparent that they simply were not a great match. Emilia was inconsistent and difficult. In bed, she was submissive but so submissive she did nothing for Kyle except lay back and let him do everything, and most frustrating to Kyle, who had learned that one of his biggest sources of pleasure was his partner’s orgasm, Emilia refused to climax. She would fight against it, squirm away, and actually say “no” while shaking her head when she got close in order to lose the sensation. Not to mention the deep jealousy Emilia had which led to many disagreements and baseless accusations against Kyle of cheating. Eventually it became too much and Emilia’s instability caused her to end the relationship.

Once again, Kyle was alone. Eight months into a separation, multiple failed, albeit short, relationships, and having come close to what he was looking for but not found it. Kyle was without much hope. Back to the same social media dating platform and the right swiping. Once again, there were many matches and chat conversations. But nothing really excited Kyle, as everyone was looking for vanilla marriage or frankly hated men in general. One user account came up of a woman named Jen who was a fiery redhead with tattoos that caught Kyle’s attention.

Her pictures were stunning, but was she real? And she was probably just another vanilla girl looking for prince charming who would be boring to Kyle. But, with some hope but no a lot of expectation, Kyle matched with Jen and began chatting. Immediately there was some connection through the chat. Something about Jen captured Kyle’s attention. She was different than most of the other women. Her confidence came through the chats even without actually being a verbal conversation. Kyle was very intrigued and the two of them began chatting all day, everyday.

Eventually one night Jen said something sarcastic and apologized by saying “sorry I am being a brat.” Now Kyle very well understood that the term “brat” had a meaning in the vanilla world as well as the lifestyle world. But Kyle also knew that women looking for lifestyle play would slip terms into regular conversations to see a reaction. Kyle decided it was time to take a shot and see what Jen was trying to say. He responded “be careful using words that have special meanings to some people,” to which Jen replied that she had used the term very much on purpose. Kyle now knew that this beautiful woman who he was forming an emotional connection with also has the lifestyle component, at least at some basic level.

Kyle and Jen decided to meet up the following Saturday. On Thursday Kyle was on a company trip a few hours away and was driving back to his house while also texting wit Jen, and the way the conversation was going so smoothly, and they way that Kyle and Jen could so easily talk about regular vanilla things like favorite foods or musicians, and then also move into talking about sexual history and desires and fantasies finally overcame Kyle and he told Jen to meet him at a brewery that night.

Kyle had laid out his sexual desires to Jen. He explained that he wanted a woman with experience and confidence and few, if any, limits. Jen explained her past and she had more people on her list (she really had a written list of names!) than Kyle had ever encountered anyone having. Over 70 men had had this girl and something about that drove Kyle crazy in the best feasible way.

Kyle did not know what to expect, but he had to meet this feasible woman of his dreams. They went to a brewery that Kyle was very familiar with and that was near Jen’s house. Kyle beat her there, because she was waiting on a grocery delivery which, frankly, Kyle wondered was a bunch of bullshit that was gonna lead to other excuses and a no show. But Kyle was happily proven wrong when his phone buzzed with a message from Jen that she was parking and wanting to know where to meet him.

Kyle walked out of the brewery’s inside seating area to the outside patio where Jen was walking through from the parking lot. Kyle instantly was blown away. Not only did Jen live up to her photos online (something more and more people simply could not say) she was far and above sexier in person than she ever hoped to be in photos. Her body was stunning with a toned figure and she was wearing tight jeans that hugged her ass in all the methods that Kyle wanted to see. They sat outside and talked for a very long time, until the brewery closed. They talked about their past, their childhood, their families, their relationships, and minutes turned to hours without either of them noticing.

Very quickly in the conversation, Kyle found his hand under the table gripping and rubbing Jen’s ankle and calf. And Jen found her hand resting on Kyle’s wrist. They began holding hands and getting lost in each other’s glance. As the brewery was closing, Kyle new that this date could not end so soon and told Jen that he wanted to take her out to another bar. They walked to her car first and when they got to her door Jen turned toward Kyle and Kyle took the opportunity to kiss her. Jen innocently, or perhaps not so innocently when Kyle reflected upon it later, said she had wanted to kiss him much earlier in the night.

They drove in their separate cars just down the street to a bar open until 2:00 a.m. and went in for a drink. They sat a table in the bar not caring who was around. They spoke openly, and not in whispers, about their sexual past and desires as their inhibitions washed away with the alcohol. Kyle was enthralled with this woman, who was the epitome of sexual confidence and experience. They both stood up to use the restroom at the same time and Kyle allowed Jen to lead the way, the entire time simply wanting to watch Jen’s ass in those jeans.

As they entered the small hallway leading to the restrooms, blocked off from the rest of the bar, Jen stopped and turned and Kyle immediately grabbed her by the back of the neck and kissed her deeply. Kyle wanted to throw her against the wall and snatch her head back and sink his teeth into her neck. He wanted to rip her sexy red shirt down off of what he already knew were perfectly firm and perky tits and squeeze, caress, lick, suck, and bite all over her chest. He wanted to put her on her knees and use her mouth for his pleasure. But it was a first date, and so Kyle kissed Jen deeply several times and they both went into their respective restrooms. On returning to the table, Jen did something that nobody had ever done for or to Kyle, and something Kyle would never forget. She did not go back to her seat at the hightop bar table they were at. Instead she stood next to Kyle and in the middle of Kyle saying something that he would never be able to remember, Jen bent down and ran her lips and tongue all over the side of his neck.

Now, what Jen could not have known at the time, was that Kyle’s next and ears were incredibly sensitive and one of his most erotic areas, and Kyle had a very real fetish around being licked. He prefered his cock to be licked instead of sucked deeply, and he could lay and let his body be licked from head to toe for hours.

Kyle knew immediately that he had to get Jen alone in some kind of privacy. He cashed out and the two left and Kyle took Jen directly to his truck. He got in the backseat, which was full of junk because he was moving. Kyle shoved all the papers and boxes to one sided and Jen immediately followed into the truck without being told or asked. This was a very good sign to Kyle that Jen was gonna be a very good girl for him.

Kyle grabbed Jen by the back of her neck and began kissing her deeply. They made out for several minutes and it began getting more and more intense. Jev was braced up in the corner of the driver’s side backdoor and the back seat and Kyle became more aggressive, working his hand inside Jen’s bra and pulling out her tits. There were just as firm and perky as he has wondered they were, maybe even more than he expected. Jen’s nipples were erect and much more pronounced than Kyle was used to.

As Kyle began squeezing and playing with Jen’s erect nipples, she began to whimper and moan. Her body reacted by her back arching and her moans began to betray her and within moments an orgasm raced through her body. Kyle stopped and stared. “Did you just cum from having your tits played with?” he asked.

“They are so sensitive.” Jen answered back quietly. Now with Kyle being one to get off on the pleasure of his partner, being a self described pleasure dom,he immediately went to work. Squeezing, sucking, biting and licking her nipples, back and forth from one to the other, while slipping in deep kisses to Jen’s mouth in between orgasms. Jen sat in ecstasy cumming from this simple act while being kissed deeply and as bar patrons walked past the truck drunkenly, no doubt at least hearing, if not seeing, what they were doing.

After about an hour of this making out session with heavy nipple play, and many orgasms for Jen, she swung a leg over Kyle and straddled him and began making out from being on top. Kyle pushed her back and as she leaned against the back of the driver’s seat, Kyle began unbuttoning and unzipping Jen’s jeans. Her tits were still exposed and he slipped his right thumb inside her panties and began rubbing her clit. Kyle was very quickly becoming mesmerized by the way her body moved and reacted to him, and the noises she made under his touch. She was exactly the sort of open, confident, and sexual he had been craving.

They both agree that it was a Thursday, and they both needed to work the next day and had to go home at some point. They parted methods, both yearning for the other’s body. Kyle with a rock hard cock having gotten no relief, but ecstatic at the way Jen’s body had convulsed while cumming from such simply touches.

They had already lined up a date for Saturday, and Kyle would make sure it was unforgettable. Jen and Kyle had talked about a great deal of sexual history and fantasies, with one of Jen’s being that she had a bit of an exhibitionist streak and wanted to be used against the large windows of a nice hotel where people could see. She said she had seen women fucked in hotel windows a couple of times in the past and wanted to be watched in that way.

Well you see, the thing about a pleasure dom who also has a successful career is that he will do everything in his power to make fantasies a reality. Kyle made reservations for a night at the nicest hotel downtown, with windows overlooking the river and city. He made dinner reservations and a superb seafood restaurant, and planned an evening without her needing to know anything. Kyle’s dominant side was certainly showing itself and as Jen was a self-described “switch” Kyle knew he would need to be clear in his dominant nature to have her back into submission.

Saturday came after a grueling 48 hours for both of them. The texts between them were rapid fire while waiting to see each other again. Kyle picked Jen up from her place in the late afternoon and took her downtown. As they checked in, they never stopped talking to each other about anything and everything. It was a relationship blossoming into something with a real connection, not just sex but also overly sexual. A mixture Kyle had craved and Jen said she had as well.

Kyle had been open and up front with his particular sharing and dominance kinks, and Jen seemed to be the girl who could roll with those without judgment or objection. Jen was clear that she did not want to jump into all of that too soon though, or at least the sharing portion, until the two of them had built a strong foundation of a relationship. Kyle appreciated where she was coming from and was blown away by her forward thinking thoughts.

Jen had also let Kyle in on some of her sexuality. First, there was this fantasy of being used against a hotel window for the city to see. She had come close, had even showed Kyle a picture of her naked in front of the hotel windows on their first date. Unfortunately for her, or fortunately for Kyle, the fantasy had never been fulfilled because the guy she had been with had some stage fright issues. Jen had left that hotel room disappointed and Kyle knew she would not be disappointed in the morning. Jen had also warned Kyle that she squirted, a lot. Kyle had been with women who squirted before and generally throwing down a towel or extra blanket fixed the issue. Jen had laughed at Kyle when he suggested this.

They made their way to their room, on the 18th floor and Kyle opened the door. Jen was still getting used to a guy who opened the doors, pulled out the chairs, and generally put her first in everything. They walked into a gorgeous hotel room with large plate glass windows overlooking the river and waterfront bars and hotels of the downtown skyline. They were very visible from here and just a few floors below them was the skydeck of one of the most trendy bars in the city, which would be filled with people all night. The room had two beds in it, which was not Kyle’s preference, he would have preferred one king size bed, but Jen had insisted that her pussy was gonna squirt so much for him that they would not be able to sleep in the bed that they had sex in. Kyle would not comprehend what she meant until later.

Kyle asked Jen if those windows were gonna fulfill her fantasy

and she smiled and said they would. She walked to them and looked out and down with a smile. They put their things away and Kyle began pulling out all of his tools and toys from his bag and laying them on the dresser. Crops, floggers, pain wheels, candles, ropes, rulers, masks, vibrators, and anything and everything else you can imagine. He had spent a very long time, and significant amount of money on this collection and he hoped Jen was impressed.

Jen walked near Kyle and Kyle grabbed her and kissed her deeply, reaching around to squeeze her ass. They walk out together and Kyle is sure to open every door, never have his hand leave the small of Jen’s back or her hand. He ordered their wine and their meals, which is mostly appetizers to keep things light. They drink a bottle of good pinot noir from Oregon and walk down the street of bars, people, and street performers to a bar/arcade a few blocks away. A night of a few more glasses of wine while bowling and playing old college arcade games had both of them very much ready to get back to the room.

They walked casually, but with a purpose as they continued to talk about every topic imaginable. They stopped and watched some street magic and Kyle even showed off a card trick or two. It was simple but a night that Kyle had never had. A night of banter and laughter, with a sexual undercurrent that was palpable. A night of fine dining, video games, and street magic. A night that organically flowed into unexpected, but amazing, events that could never be recreated in exactly the same way.

The door to the hotel opened and Kyle led Jen inside. “Take off your clothes.” Jen immediately complied and stripped to nothing but a chain necklace that she was wearing that could double as a collar and leash. She stood naked in front of the windows, with every light in the room on and the darkness outside revealing her to the entire city, especially the bar below packed with people.

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