Vacation Bound

A weekend on the coast

We really needed to get away for a few days along. Life has a way of beating you down if you don't make time for yourself to unwind every so often, and both my wife, Gwyn and I were starting to burn the candle at both ends. Work, volunteerism, kids, and even social activities were all starting to feel like a burden, so when I suggested a week away together the idea was met with a lot of enthusiasm. We started to talk about what kind of a vacation we were needing, and I suggested to Gwyn that she plan something to her specifications, and that my only hope was that she would add in some form of 'surprise' for me.

The invitation to create 'surprise' was always an inherently sexual idea, and Gwyn knows my kinks and quirks quite well. She is generally willing to go along with most things when I bring them up, but is often unwilling to lead our play, and one of my most prominent kinks is that I am almost entirely sexually submissive. Asking Gwyn to lead a surprise would usually create an uncomfortable level or anxiety in her, and sometimes backfires into an unwillingness to take charge, but this time it was different.

Gwyn immediately agreed to taking charge of booking our time away, as well as creating a 'surprise' for me. She stated right away that "I've had an idea percolating in my mind for a bit, and this might be a great opportunity to make it happen."

I was intrigued, and excited by the idea, but certainly not worried at all as I would trust Gwyn not only with my life, but with my mental health, my secrets, my passion, and my heart. I knew that she would take care of me regardless of what her idea was, and that with her in charge we would have a great time both in terms of a break from reality, and also in having a sexual moment to bring us closer and deeper in our togetherness. Little did I know exactly how far down the rabbit hole she would take me.

The night we had the conversation about getting away, we were both feeling horny, and we managed to take an hour to ourselves to fuck and talk and play. She was goading me about our vacation while she rode my face to her orgasm, and then planted herself on my hard cock and rode and teased me until I came as hard as I had in months. Once I was sated, she slid up my chest and turned herself around and planted her ass on my face so that I could lick her deeply. I could taste her orgasm, and I think a little of mine, as she ground her ass on my tongue and rode herself to her second orgasm of the night.

When she collapsed next to me, and curled un into a spoon behind me, she whispered in my ear, "I'm looking forward to our time away. I know just the place, and I'm looking forward to treating you how you really want to be treated."

We slowly moved on, got dressed, and went back to our regularly scheduled lives for the next couple of months until the day arrived to leave on vacation.

Vacation day

The kids were planned for, jobs arranged, meetings rescheduled or cancelled, so we knew that from the moment we got in the car to leave we were free. Gwyn even instructed me not to pack my own bag, and said that she would pack everything I needed. In the trunk of the car was a large suitcase, our tennis racquets, my golf clubs, and a couple of extra pairs of shoes.

The only thing that happened that morning that leaned into anything sexual, was that when we were getting dressed in the morning, Gwyn gave me a new pair of thong panties and told me to put them on for the day. I enjoy crossdressing and we have played around that way occasionally, but she had never taken initiative in dressing me or asking me to dress. Crossdressing happened when I made it happen, and she was content to play along. When I was sliding the thong up my legs and tucking in my shirt to avoid accidental 'whale tail', I was excited to think that maybe there was lingerie and some women's clothes in my near future, but I kept that thought to myself, knowing that surprises are more fun when they are actually surprising.

We finished dressing and I loaded the car, and away we went. I knew that we were not flying anywhere, and that we were a couple of hours away from our destination, so I presumed we were heading somewhere on the coast. The drive was largely uneventful. We made good time, stopped for gas once, and drove into one of the cute little towns along the coast right about noon. Gwyn suggested we stop for a bite at a café just off the main road, and I easily agreed. It was perfect timing on the way to whatever Air BnB or VRBO place we were heading towards.

We entered the café and found a booth, and were just about to order some food when a woman came up to our table and introduced herself to Gwyn.

"Hello. You must be Gwyn. I am Lenore. I believe you were expecting me."

She didn't pay me the slightest bit of attention, and continued the conversation purely with Gwyn.

"Our mutual friend assures me that you both can and will be completely discreet. Do you agree to not share anything about me with anyone without my explicit permission, and to honour the terms of our agreement that me made over the phone?"

I smiled inwardly, assuming that her presence here was part of the surprise portion of our vacation.

Gwyn responded to the question with a somewhat meek, "Yes we do."

Lenore continued, "And do you speak for him as well. Can you be certain of his complete discretion?"

"Yes, absolutely," Gwyn replied.

"Excellent," Lenore stated. "Then I will sit and join you. You may move to the other side and sit beside your husband. You should make him stand so you can sit beside the window."

Once we were arranged per her instructions, Lenore continued speaking - to both of us this time. "I am Mistress Lenore. I will be in charge of the first portion of your vacation here on the coast. I have been employed for two days to act in my role as a professional dominatrix, to work with you both and teach you, Gwyn, how to properly and completely control and command your husband in all things sexual and more. I will teach you the art of domination, and science of control. If you listen, and commit yourself, I will leave you in two days having a much better sense of how your submissive husband would like you to control him. I will teach you how much power you have in your relationship, and how to wield it kindly, gently, and fiercely.

I will also work to teach your husband that submission can be about far more than just sex, and that acknowledging his willingness to be dominated sexually is just the beginning. I will teach him how to be a better husband, partner, lover, and friend. I will show him what it is like to submit completely, and find out if that is truly what he desires of his life, or if it is just a sex game that is limited to the bedroom.

I will work with you both to find the limits of your commitment to one another, as well as the limits of the physical pain and pleasure that are available to you if you decide to go further down the path towards a real female led relationship.

Does this sound good to you Gwyn? Is this all truly why you hired me?"

Gwyn sounded somewhat sheepish when she replied, "Yes," and after a few seconds she added "Mistress Lenore."

Lenore looked at me for the first time with any significance and asked me as well, "Does this sound good to you. Do you want to genuinely submit to Gwyn, and are you willing to submit to me in order to learn how fully you must commit to your submission to make it real?"

It took me a minute to gather my thought, and assess my situation, and stifle the level of arousal I was feeling about the entire conversation so far. I had doubts, about both my willingness to give myself over to submission fully, and about Gwyn's ability to take charge as fully as I wanted her to. I looked our guest in the eyes, and sunk fully into them. I imagined what it would be like to allow this woman complete control of my life for a time, and allow her access to my deepest secrets. It took a moment, but the words that came to me, and that I spoke out loud were "Yes Mistress Lenore."

"Good," Lenore stated. "I'm glad it took a moment to think through things, and though there may be things in the next few days which I need to punish you for, I will never hold those moments of hesitation against you.

That said, for the next two days you will both do whatever I ask of you without hesitation or question. You will obey my every whim in an instant, and if you have questions afterwards, I will provide you an opportunity to ask them when I see fit. I will take charge of these first couple of days of your vacation and make them my own."

Mistress looked at me and pulled a small pink box from her purse. "This gift is for you. Please take this gift, go to the bathroom and open it in one of the stalls. Use all the pieces of this small gift, which includes a new lovely pair of panties for you, and throw your underwear in the garbage and return to the table. Pay the bill, and get in your car and follow me in mine. I will lead you to your vacation home, and you may stay in the car by yourself until I come to get you. Do you understand?"

I hesitated just a moment, hardly noticeable, but Mistress noticed of course. The hesitation was not about the instructions, or doing whatever I was asked, but I didn't want to throw out the new panties Gwyn had given me that morning. I was about to ask her to allow me to save them, when Gwyn spoke up. "I think he is hesitating because he is already wearing panties that I gave him as a gift this morning. Perhaps he could change and bring them back to you to show you."

Lenore glared at Gwyn. "You will be punished for questioning my orders." And then she looked at me. "You will be punished for your hesitation - but now that I know the issue, you will be allowed to keep the gift. You will bring your current panties to me in my car before we drive away."

I stood and took the box from the table and went towards the bathroom, leaving Gwyn and Lenore at the table to sort things out. In the bathroom, I went to a stall and opened the box. There were a pair of black latex panties with a cut out in the back. They were the kind of thing that Mistress Lenore might use so that she had easy access to my asshole if she wanted to fuck me without anything in the way. The other part of the gift was a bejeweled steel butt plug and a single use package of silicone lube. I had used plugs on occasion, fantasizing about Gwyn fucking me in the ass, but this plug was larger than anything I had previously played with. I stripped off my pants and my new pink thong, sat down, opened the lube and used my fingers to lube my asshole. I covered the plug with the rest of the lube and started to slowly work it inside of me. I was about to cry out a little when the plug finally popped past my sphincter and settled into place. Once I took a moment to get used to the full feeling in my ass, I stood up and put on the latex panties. They fit well, but were very snug and a little uncomfortable around my cock and balls. I took a moment to leave the stall and check out my ass with the plug and panties, and I couldn't help but gasp a little at the sight. I was a little anxious about what the next couple of days might hold, but I really couldn't wait to get started. I pulled up my pants, washed my hands and threw aware the garbage, and put my pink thong in the gift box to give to Mistress Lenore.

When I left the bathroom, I returned to the table and grabbed the bill. Walking was not uncomfortable, but I did feel every step and I felt like I was swinging my hips a little more than normal. I paid the bill at the counter and left the restaurant. I looked around the parking lot a found Mistress Lenore and Gwyn in a cute red Fiat, and approached the driver's side. Mistress Lenore rolled down the window and accepted my gift and opened it immediately, taking the thong from the box and giving it to Gwyn, instructing her to keep it in her mouth for the drive.

I went back to our car and once I had adjusted for a moment to sitting on the new toy in my ass, I started the car and followed the red Fiat out of the parking lot.

I was surprised as I followed the Fiat that we were heading inland, not along the coast. Both Gwyn and I generally like to stay on the oceanside when we are on vacation and able to manage it. It took about 20 minutes to reach our destination, and the steep driveway led into a forested cottage that looked like a classic west coast getaway spot. Mistress Lenore came to my window once I was parked and instructed me to bring our luggage and hers into the entryway of the cabin, and then lock her car and sit quietly in mine. She would come to get me when she was ready for me.

I moved all of the luggage, and never heard a peep from either of my two guides, and once everything was moved and nicely organized, I returned to the car. I was intrigued at how much luggage Lenore had for a short two-day trip, but made myself excited thinking of what the contents of her three bags might include. When I sat back down in the car, I had to shift around a couple of times to make the plug in my ass more comfortable, and I found that as I shifted, I was aroused by the feel of the assless latex I was encased in.

After about 20 minutes, Mistress Lenore approached the car. She had changed clothes entirely, and was wearing a black leather dress and corset, her pale white breasts pushing up and out of her top. Her dark hair was pulled back into a ponytail, and she wore a remarkable pair of black patent heels. Her lips were a deep red colour, and she licked them as she approached the car to retrieve me.

"Come with me." I opened the door and followed behind her as she walked away from me. I admired the sway in her leather covered ass, and how beautiful she was in all of her power and control.

We entered the cabin and she took a moment to observe the well-organized luggage and thanked me for being so attentive to the detail of organizing the luggage appropriately. She showed me a door with a deadbolt leading off from the living room, and told me that it led to the basement. She commanded me to put her luggage in the master bedroom upstairs, and then return to the living room and strip down to my panties and plug. I was to fold all of my other clothes and place them on the couch in the living room, and then open the basement and silently go downstairs, closing the door behind me. Once I was downstairs, I was to sit silently in the chair in the middle of the room and wait for further instructions.

I obeyed every order, did everything as perfectly as I could imagine, and resisted the immense temptation to look in Mistress Lenore's luggage. When I stripped in the living room, I folded all of my clothes as well as I could and placed them tidily on the couch. I opened the door and could feel that it was very heavy, solidly built, and swung very precisely when it opened. I could hear regular sounds like a smack, and occasional moans coming from the basement, and again I was getting more turned on as I closed the door and moved myself down the stairs towards the sounds. When I entered the basement room, I found it was a dungeon, with a significant collection of bondage apparatus, sex toys, benches, a single chair in the middle of the room, and my wife hung from the ceiling with her arms above her, and her feet in heels barely touching the floor.

Gwyn was cuffed, and completely naked, and her ass and back were bright red with stripes. I sat down in silence and observed Mistress Lenore lightly, but insistently, taking the flogger to Gwyn over and over again. Gwyn moaned lightly with every blow.

Mistress stopped and looked and me and spoke. "How much would you love it if I allowed you to worship Gwyn's ass right now while it is all bright and red and hot? Would you get down behind her and push your tongue up into her, bringing her off while she is hanging there helpless? Do you imagine yourself getting up behind her and fucking her hard while she is bound from the ceiling? Or do you imagine yourself trading places with her, and it is you that is bound and helpless, and you that is being fucked and licked and flogged while she and I surround you and do anything we want with you?

Both are going to happen over the next couple of days, but for right now Gwyn is going to remain right where she is and you get to observe as I punish her. I want you to sit still, so I am going to bind your arms behind you on that chair and I'm going to gag you so that you remain silent. Then I am going to take a cane to your wife's ass and upper thighs leaving dark red stripes across her. This is her punishment for interrupting me in the café when I was instructing you to go to the bathroom and change. I told you both that I understood the reason, but reasons are not good enough to avoid discipline."

Mistress Lenore took cuffs from the wall and bound my arms behind me, and then took a ball gag and put it into my mouth and connected it around my head to keep me silent. The silicone ball stretched my jaw, but after a couple of moments I settled into the discomfort and just enjoyed the feeling of being bound in this scene.

"Once I have caned Gwyn five times, and given her marks to remember who is in charge for the next two days, it will be your turn. I will allow your wife to flog, spank, and eventually cane you as it was your hesitation that caused her interruption. You will both learn to obey without question, and Gwyn will learn that discipline is undeniable. If you carry on with her as your Mistress, and not just your wife, she will punish you for every transgression, and will always insist on your complete and willing obedience to her whims."

With that, Mistress Lenore took a cane from the wall and moved to the side of Gwyn, rubbing the cane gently over her hot red ass, and suddenly came down hard leaving a bright red stripe directly across Gwyn's ass. In short order, there were four more stripes, and Gwyn was lightly sobbing as Lenore reached up and disconnected the cuffs that were holding my wife to the ceiling.

They hugged, Mistress Lenore in her black leather, and Gwyn completely naked except for her heels. Lenore rubbed Gwyn's ass gently, and ran her hands across Gwyn's exposed breasts and nipples. Lenore took a moment and held Gwyn's face still and kissed her lightly and tenderly on the cheek and then the lips, leaving a red kiss mark on her cheek. She then spoke to Gwyn.

"Are you ready to discipline your husband for the hesitation that that was the cause of your punishment. Are you ready to take your control of him to the next level?"

Gwyn looked at me and smiled, and looked at Lenore and quietly said, "Yes."

Lenore uncuffed me, leaving the gag in my mouth, and led me to a raised bed and leaned me across it. She pulled my arms across the bed and cuffed them on the other side so that my latex-pantied ass was exposed to the room. She spread my feet apart and cuffed my feet to a bar which kept them spread apart almost as far as possible, and then raised the bed a little higher to the point that I had to stay on my tiptoes in order to maintain balance and connection to the floor.

I was hardly even in place when I felt the first stroke of the flogger. Gwyn was to my side, repeatedly and firmly giving me strokes with the same flogger that had been used on her. I could feel the heat as my ass reddened, and feel the sting as the back of my thighs got the same treatment. After a while the flogger stopped, and Gwyn showed me a leather paddle with the word 'Slave' on it. She didn't really hesitate before bringing that down on my ass and giving it a further reddening. I moaned with every stroke that hit me, and thought to myself how often I had fantasized about Gwyn paddling me for my disobedience, or disciplining me in this way. She worked her way down one leg and back up the other one, even taking a brief moment to tug and push on my plug as she ran her hand across my ass.