I was at work and went to make a call on my cell phone when a photo memory popped up. It was a picture of my girlfriend, Sasha, from the Halloween party in Key West, called Fantasy Fest.
Fantasy Fest is a ten-day party in Key West, usually held during the last week of October. It is a place where adults gather and simply kick back not caring about the folks at home that are too inhibited to have a fun adult time. There are essentially no limits on what people wear for costumes. Some people will be covered in body paint from head to toe while others don't dress up at all. Many women are topless and others will wear their skimpiest lingerie. There is one woman who is there every year that takes a string and wraps it around her waist down her butt crack, and centered on her pussy. I would call this the ultimate G string. Everyone is here to have fun, if you were there and didn't have fun, you probably should have stayed home with those other inhibited people.
On the second night of this year's fest, we decided to dress up as Dom and sub. I was the Dom and Sasha was my sub. I wore black leather shorts that had a tare away pouch on the front with a leather vest to match.
We dressed Sasha up a little more extravagantly, after all, it is clearly all about the sexy ladies. We started with a heavy leather collar that was basically black but it had red trim and large loops for her leash. She wore black thigh high boots that laced up the back with a five -inch spike for a heal. This was complimented by a black leather body harness that went from the collar, circled around her 36C tits, leaving them completely exposed, and finished off as a very narrow thong that was only about an inch wide. Both of her nipples are pierced so she put some large jewelry on just to add a little bling.
She looked fucking hot; I clipped on her leash and told her she will do as she is told. She said, "Yes sir"
She reached for my dick only to find it very stiff and said, "I guess you like."
I said, "More than you can imagine, now let's go show you off." Once we were out on the street several people admired her outfit but as sexy as it was, she fit right in.
In real life, Sasha is a very respected partner at an international accounting firm. Her self-esteem is not an issue in any regard as she is confident in herself both professionally and in her personal life. Unfortunately, she needs to protect her identity when she is walking on the streets of Key West, nearly naked. Typically, she will get her picture taken hundreds of times and we expect she will appear on the internet but we don't need any of those shots showing up in the board room or maybe worse yet, the wash room. We found a black hood that has openings for her eye, mouth and nose. The challenge was to fund one that would not be too hot to wear all evening. We were successful in our search and the added mystery of her identity made it that much more interesting.
She is a beautiful woman, five foot six with a very pretty face, short black hair, gorgeous boobs, long shapely legs and an ass that completes the package. She is the type of women that as soon as you see her the first thing that comes to mind is, oh how I would like to do that.
I brought a riding crop with me because a common thing for the ladies to do is when two ladies dressed as subs meet, they will pose for pictures slapping each other on the ass. She asked what the crop was for and I told her "when you meet up with another lady who is going to smack your ass, give her the crop, it will make it more fun."
Sasha said, "For who, it will be me getting the sore ass."
I said, "Just try it and if it hurts, we will get rid of it." I smack her ass, she jumped but also smiled.
She said, "That wasn't bad, ok, it might be fun."
Anyway, back to the story, I texted the picture to her and she responded immediately with a happy face and commented," That was so much fun, can we do it again."
I responded, "Your assuming we are going to Fantasy Fest again this year."
"No, I meant, now," she followed with a happy face.
I said, "That would be fun but where were you planning to go."
She said replied, "How about the basement, we could call it the dungeon."
So now my dick jumped to attention and I can't begin to imagine what got into her.
I texted back, "We can talk about it, I have a conference call I have to be on."
She said, "Too bad, this was just starting to be fun. Luv U."
I got on my conference call and to be honest, I was having trouble concentrating thanks to my text conversation with Sasha. After about twenty minutes I got another text from Sasha, this time it was a link to an adult web site's wish list. I opened it on my phone and found that she had made a wish list of bondage products. The first few items were simple things like handcuffs, ankle cuffs, flogs, ball gags and hoods. But then she got into some really funky stuff like a St. Andrews cross, a bondage fuck bench and other sex furniture. There was also some suspension equipment.
Needless to say, my concentration on my call was shot, I have no fucking idea what they were talking about.
Sasha and I had talked about doing some experimenting but clearly, we need to talk further.
I sent her a text, "Interesting, sounds like we have some things to talk about."
She responded, "😊 can't wait, see you tonight."
When I got home, she was already there. She greeted me at the door with a big hug and a kiss along with a cold beer. She said, "Can we go out on the deck and talk?"
I said, "Of course."
We sat down on the swing together and I said, "So you want to get cuffed and flogged."
She gave me a big smile and with no hesitation, she said, "Yes, I do." Clearly, she was excited, "I don't want to get beaten or hurt bad but a good spanking is a turn on."
I said, "I know we had some fun in KW with this but, what got you going today."
Sasha said, "I have been thinking about it and doing research ever since then." She continued, "You know when I had the flog in KW and I gave it to other girls in similar outfits and we playfully flogged each other."
I said, "Yah, and it was so sexy."
"Well", Sasha said, "Some of it was not so playful. A few of those girls whipped me pretty hard but you know I did the same to them."
Feeling puzzled, I said, "Where was I?"
She said, "A couple times you were right there and didn't realize what was going on and the best part was that I had two orgasms as a result of being whipped. One time, the other girl turned me sideways and had her fingers on my clit while she flogged me. It was the most intense orgasm I have ever had."
I said, "And I missed all this."
"My pussy was dripping the entire evening."
"Why didn't you tell me?"
She looked down and said, "I was a little embarrassed."
I asked, "So why are you telling me now?"
With confidence she said, "Because I can't get it off my mind and it was as exciting as hell. I'm ready to give it a try."
I said, "So you want to make a dungeon?"
"We can start out real small and expand if we like it." She said with enthusiasm.
We went downstairs to check out our new dungeon. Sasha said, "There is one thing that I really would like to have." She hesitated a bit and said, "A St. Andrews cross, it could go right there."
I was a little taken back by her boldness but said, "I have to admit, I really don't know what a St, Andrews cross is, can you describe it for me?"
Sasha explained, "It is a heavy wood cross that goes from floor almost to the ceiling. They can be straight up and down or some lean back, I think I want one that can be leaned back. They have shackles of some sort for each hand and ankle leaving the person standing spread eagle.
I said, "Interesting."
She went on, "The person that is bound to the cross can either face it or face away from it leaving the person vulnerable in different ways."
I said, "We could do that."